Natural sweetener

ABSTRACT

The invention relates to extracts, in particular non-nutrient phytochemicals, form sugar cane or sugar beet waste products, such as molasses, sugar mud and bagasse, which have Glycemic Index (GI) lowering properties and their use as sweeteners and in foods containing sugar.

CROSS-REFERENCES TO RELATED APPLICATIONS

This application is a continuation of U.S. application Ser. No.11/628,151 filed 27 Dec. 2006, which is now issued as U.S. Pat. No.8,138,162 and is a national stage application corresponding toPCT/AU2005/000798, filed 3 Jun. 2005.

FIELD OF THE INVENTION

The invention relates to non-nutrient phytochemicals having desirableproperties and health benefits. More particularly the invention relatesto non-nutrient phytochemicals which lower the glycemic index of foodssuch as sugar. The invention also relates to an improved sweetener. Moreparticularly, the invention also relates to a sucrose product comprisingadded non-nutrient phytochemicals and having a lower glycemic index.

BACKGROUND OF THE INVENTION

In this specification, where a document, act or item of knowledge isreferred to or discussed, this reference or discussion is not to betaken as an admission that the document, act or item of knowledge was atthe priority date (i) part of common general knowledge; or (ii) known tobe relevant to an attempt to solve any problem with which thisspecification is concerned.

Fundamentals of Good Health and Nutrition

Nutrition is usually considered from the perspective of the relationshipbetween food and human health. Good nutrition:

-   -   involves ensuring that all the essential nutrients are        adequately supplied and utilized to optimize health and well        being;    -   is essential to growth, reproduction and maintenance of normal        body function; and    -   is also essential for optimal activity, resistance to infection        and repair of damage or injury.

Until recently, nutritionists have focused primarily on the nutrientelements in foods. Nutrients in foods have historically been classifiedinto macronutrients (protein, carbohydrate, fat) and micronutrients(vitamins, minerals, water and essential elements). However, food isalso composed of non-nutrient factors or phytochemicals, which are nowthought to have their own beneficial effects, such as reducing the riskof cancer or heart disease.

No single substance is sufficient to maintain adequate health. For thisreason, a variety of foods are needed in a diet to assist with deliveryof a broad array of micronutrients, macronutrients and non-nutrientplant components (also known as phytochemicals). Some specific nutrientsare known to be singly effective, eg fibre, however, most nutrients workmore effectively when combined with other dietary components and thebody's own chemical products, enzymes and co-factors, to enableabsorption and utilization. Phytochemicals (substances found in plants)are important components of food that are likely to be essential foroptimal health. The main classes of phytochemicals found in fruit andvegetables include plant sterols, flavonoids and sulfur-containingcompounds. Nutritional science has begun to focus more on the role ofspecific foods and food phytochemicals in reducing the risk of diseasessuch as obesity, diabetes, arthritis and other chronic non infectiousdiseases such as osteoporosis, high blood pressure, high bloodcholesterol, cancer and health problems like migraine and menopausalsymptoms. Examples of phytochemicals and their postulated healthbenefits are as follows:

-   -   Anthocyanins/Proanthocyanidins are found in berries, cherries,        red grapes, plums and red-cabbage and are thought to protect the        heart, lungs and blood vessels.    -   Bioflavonoids (e.g., Taxifolin, Rutin, Ellagic Acid, Quercetin)        are found in citrus fruits, black tea, red wine, onions,        tomatoes, apples, potatoes, grapes and broad beans and are        thought to be an antioxidant and have anti-cancer benefits.    -   Carotenoids (e.g. Lycopene, Lutein, Capsanthin) are found in        carrots, mangos, peaches, pumpkin, squash, sweet potatoes,        tomatoes and dark leafy green vegetables and are thought to have        anti-cancer benefits.    -   Catechins (e.g. Epigallocatechin Gallate) are found in green tea        and apples and are thought to be antioxidants and have        anti-cancer benefits.    -   Glucosinolates (e.g. Sulphoraphane Sinigrin Isothiocyanate) are        found in broccoli, brussel sprouts, cabbage, kale and watercress        and are thought to have anti-cancer properties including the        ability to reduce the growth of pre-cancerous cells.    -   Organosulphides (e.g. Allicin) are found in garlic, onions and        leeks and are thought to help fight stomach cancer and reduce        LDL cholesterol.    -   Phytoestrogens (e.g. Isoflavones, Lignans) are found in soy        beans, flax seeds and berries and are thought to protect against        breast cancer, prostate cancer and menopause symptoms    -   Bromelain is found in pineapples and is thought to have        blood-thinning properties.    -   Capsaicin is found in chilies and is thought to be an        antioxidant and pain-reliever.    -   Chlorophyll is found in wheat grass, seaweeds and dark green        vegetables and is thought to have anti-cancer and antiradiation        properties.    -   Coumarins are found in tomatoes, green peppers, strawberries and        carrots and are thought to have blood-thinning benefits.    -   Papain is found in papaya and is thought to help relieve pain.    -   Resveratrol is found in red grapes and is thought to help        protect against heart disease.

US patent application no 2003198694 teaches that antioxidant compoundscan be extracted from natural sugar cane and beet which can be used inthe production of functional food products. The antioxidant compoundsdisclosed by the inventors include polyphenols and flavonoids.

Glycemic Index

The glycemic index (GI), invented in 1981 by David Jenkins and ThomasWolever of the University of Toronto, is a new system for classifyingcarbohydrate-containing foods, according to how fast they raiseblood-glucose levels inside the body. In simple terms, a food with ahigher GI value raises blood glucose faster and is less beneficial toblood-sugar control than a food which scores lower.

The GI consists of a scale from 1 to 100, indicating the rate at which50 grams of carbohydrate in a particular food is absorbed into thebloodstream as blood-sugar. Glucose itself is used as the main referencepoint and is rated 100.

The GI separates carbohydrate-containing foods into three generalcategories:

-   -   High Glycemic Index Foods (GI 70+) causing a rapid rise in        blood-glucose levels;    -   Intermediate/Medium Glycemic Index Foods (GI 55-69) causing a        medium rise in blood-glucose; and    -   Low Glycemic Index Foods (GI 54 or less) causing a slower rise        in blood-sugar.

The glycemic load (GL) ranks foods according to actual carbohydratecontent and indicates how much carbohydrate is in a standard servingsize of food. To calculate glycemic load in a typical serving of food,divide the GI of that food by 100 and multiply this by the useablecarbohydrate content (in grams) in the serving size. For example, theglycemic index of carrots is about 47. Carrots contain about 7 grams ofcarbohydrate per 100 g of carrots. So, to calculate the glycemic loadfor a standard 50 g serving of carrots, divide 47 by 100 (0.47) andmultiply by 3.5. The glycemic load of carrots is therefore 1.6. Severalfactors influence how fast a particular carbohydrate food raises bloodsugar. These factors include: the chemical and physical structure of thecarbohydrate-food in question; how refined the carbohydrate is; how thecarbohydrate is cooked; and also the presence of other substances whichreduce either the potency of the body's digestive enzymes, or the speedof digestion. Each of these factors is discussed further below.

-   -   Chemical structure of the carbohydrate: For example, the body        processes glucose very efficiently, but the body cannot easily        metabolize fructose, a common monosaccharide in fruits, which is        why fructose has a low GI of 23. Ordinary table sugar (sucrose),        is a disaccharide made up of one molecule of glucose linked to        one of fructose. Hence the glycemic index of table sugar is 65,        midway between 23 and 100 in the medium-glycemic-index range.

-   -   Physical structure of the carbohydrate: For example, most breads        are in the high range—not due to the chemical nature of wheat        starch, but for two physical reasons. (1) The fine particle size        of wheat flour gives digestive enzymes great surface area to        attack and metabolize the bread. (2) The surface area of bread        is also increased by its puffed-out, fluffy structure. The        glycemic value of bread is significantly raised by these        structural attributes.    -   Level to which the carbohydrate is refined: One of the most        important factors that determines the GI of carbohydrate foods        is how refined or processed are the carbohydrates. In general,        refined or processed carbohydrates have had most of their        ‘natural’ fiber and other ‘inconvenient’ constituents (e.g.        which may affect the food's shelf-life) removed. The        carbohydrate is incapable of resisting the digestive enzymes and        is rapidly metabolized into glucose.    -   Extent to which the carbohydrates are cooked or prepared: Pasta        has a medium-GI value of 40-50. This can be further reduced by        cooking it less (al dente). This is because al dente pasta        resists the effect of digestive enzymes more than regular cooked        pasta and so has a lower GI.    -   Fiber slows down metabolism and digestion of carbohydrates:        Fiber (either in the carbohydrate itself or in the stomach)        protects the starchy carbohydrate from rapid attack by digestive        enzymes, or slows digestion in the digestive tract. Either of        these consequences will slow down the conversion of the        carbohydrate to glucose.    -   Fat and/or acid slows down metabolism and digestion of        carbohydrates: The more fat or acid a carbohydrate food        contains, (or the more fat or acid in the stomach during        digestion) the slower the carbohydrate food is converted to        glucose and absorbed into the bloodstream. The presence of fat        and/or acid retards the emptying of the stomach. An increase in        acid can be achieved by adding vinegar or lemon juice to the        diet.

The GI of many foods has been assessed. Honey has a broad GI dependingupon the type. Romanian locust honey for example has a GI of 32 whereasCanadian honey has a GI of 87. Foods containing longer chaincarbohydrates-fructo-oligosaccharides such as Jerusalem artichokes havea GI of 0. Fruits also contain carbohydrates but some are low GI andsome are high GI. Apples have a GI of 38 and watermelon 72.

Issues Raised by High GI Diets Include the Following.

-   -   High-glycemic-index foods trigger strong insulin responses,        thereby exposing the body to all the negative effects of        insulin. By comparison, low-glycemic value foods do not provoke        this insulin response.    -   Diets containing high-glycemic-index meals, which cause rapid        and strong increases in blood-sugar levels, have been linked to        an increased risk for diabetes.    -   Over-consumption of high-glycemic-index carbohydrates may        aggravate insulin resistance in patients predisposed to the        condition. Insulin resistance (called Metabolic Syndrome X, or        more properly, Insulin Resistance Syndrome) is believed to be a        precursor of type II diabetes.    -   Insulin resistance is believed to be a genetic condition,        aggravated by obesity. However, some experts consider that it        may be the result of a separate inherited sensitivity to        high-glycemic-index carbohydrates.    -   Lower glycemic index diets have been shown to help control type        II diabetes and reduce symptoms of insulin resistance.    -   High-glycemic-index diets have also been linked to an increased        risk for heart disease.    -   Over-consumption of high-glycemic-index foods has also been        linked to food cravings and disordered eating patterns as a        result of repeated surges and falls in blood-glucose (“sugar        spikes”).

Low GI Diets

It is now thought that individuals who are susceptible to type IIdiabetes and coronary heart disease should follow a low GI diet. It hasalso been found that following a low GI diet can assist individuals withdiabetes to manage their sugar levels and it can assist individuals withobesity problems to control food cravings, reduce appetite swings andimprove eating habits.

One example of an attempt to lower the GI of foods is disclosed ininternational patent application no WO2004/014159. The method disclosedinvolves administering an effective amount of flavonoids which inhibitthe action of the enzymes (eg α-amylase) which break down carbohydratein the intestine, thereby inhibiting the rate at which glucose isreleased into the bloodstream.

Sugar

Sugar is a common carbohydrate used in food because of its sweet taste.

After being mechanically harvested, sugar cane is transported to a milland crushed between serrated rollers. The crushed sugar cane is thenpressed to extract the raw sugar juice, while the bagasse (leftoverfibrous material) is used for fuel. The raw juice is then heated to itsboiling point to extract any impurities and lime and bleaching agentsare added and mill mud is removed. The raw juice is further heated undervacuum to produce bulk sugar crystals and a thick syrup known asmolasses. The two are separated by a centrifuge and the molasses wastestream is collected for use as a low-grade animal feedstock. The bulksugar crystals are further refined to increase their purity.

The bulk sugar crystals from the process shown in FIG. 11 are furtherrefined to produce the many commercially available sugar products. Thebulk sugar crystals are mixed with a hot concentrated syrup to softenthe outer coating on the crystals. The crystals are recovered bycentrifuge and then dissolved in hot water. This sugar liquor is thenfurther purified by carbonation or phosfloatation, filtration,decolourisation and then seeded with fine sugar crystals. Once thecrystals have grown to the requisite size, the crystals are separatedfrom the syrup by centrifuge, dried, graded and then packaged. There maybe several repetitions of recovering sugar crystals from the sugarliquor. The dark sugar syrup which is left after all of the sugarcrystals have been recovered is also called molasses.

Almost all of the commercially manufactured sugar is white andgranulated. White graded sugar is 99.5% sucrose and is made up ofcrystals averaging 0.6 mm. Caster sugar has an average crystal size of0.3 mm. Icing sugar is produced by crushing white sugar in a specialmill to produce a fine powder.

There are also a range of non-white sugar products. Coffee sugar is alarge grained, brown flavoursome crystal which is produced using thesyrups left after extracting the white sugar crystals. Raw sugar is astraw-coloured granulated sugar produced from sucrose syrups whichcontain some residual colour and flavour from the sugar cane plant—it isspecially selected and handled to ensure a hygienic product. Goldendemerara sugar is a premium raw sugar produced from selected syrupswhich imparts a rich caramel taste to food. Brown sugar is aflavoursome, fine-grained and moist crystal produced by furthercrystallization of the extracted dark coloured sucrose syrups producedin the separation stages of the refining process.

The syrup left after white sugar has been removed is used to make goldensyrup and treacle. These syrups are made in a similar fashion with thedifference being that golden syrup is decolourised whereas treacle isnot.

Approximately 70% of the world's sugar comes from sugar cane and about300% comes from sugar beets. Similar processes are used to manufacturesugar products from sugar beets. However, it is a single step ratherthan two step process.

The beets are harvested in the autumn and early winter by digging themout of the ground. Because the beets have come from the ground they aremuch dirtier than sugar cane and have to be thoroughly washed andseparated from any remaining beet leaves, stones and other trashmaterial before processing. The processing starts by slicing the beetsinto thin strips/chips/cossettes. This process increases the surfacearea of the beet to make it easier to extract the sugar. The extractiontakes place in a diffuser where the beet is kept in contact with hotwater and the resultant sugar solution is referred to as the juice. Theexhausted beet slices from the diffuser are still very wet and the waterin them still holds some useful sugar so they are pressed to squeeze asmuch juice as possible out of them. The pressed beet, by now a pulp, issent to drying plant where it is turned into pellets which form animportant constituent of some animal feeds. The juice is then cleaned upbefore it can be used for sugar production and the non-sugar chemicalsare removed in a process called carbonation (milk of lime (calciumhydroxide) and carbon dioxide gas). The calcium carbonate (chalk) whichforms traps the non-sugar chemicals and is removed (called mud) in theclarifier. Once this is done the sugar liquor is concentrated untilsugar crystals form. Once the crystals have grown the resulting mixtureof crystals and mother liquor is spun in centrifuges to separate thetwo, rather like washing is spin dried. The crystals are then given afinal dry with hot air before being packed and/or stored ready fordespatch. The final sugar is white and ready for use. Because one cannotget all the sugar out of the juice, there is a sweet by-product made:beet molasses. This is usually turned into a cattle food or is sent to afermentation plant such as a distillery where alcohol is made.

Table sugar is 99.5% sucrose, the most biologically abundantdisaccharide. Saccharides are simple carbohydrates classified asmonosaccharides, oligosaccharides or polysaccharides depending upontheir structure. Sucrose consists of glucose and fructose bound by aα-1,2-glycoside bond and is sourced from both sugarcane and beets. Asdiscussed above, sucrose has a GI of about 65.

One of the most difficult dietary changes faced by someone who has tochange to a low GI diet is to reduce the amount of sugar which theyconsume. This is usually achieved by replacing the sugar with artificialsweeteners such as aspartame. However, artificial sweeteners havedrawbacks, including their unnatural taste.

Fructose

In an attempt to provide low GI foods, many people started usingfructose as a sweetener instead of sucrose/table sugar. As mentionedabove, fructose has a low GI of 23 and thus had benefits for diabetics.Fructose is readily available as corn syrup and in addition to use bydiabetics it is being used in a variety of food, drink and confectionaryaround the world. However, there are now concerns that consumption offructose as a sweetener has detrimental effects including

-   -   increasing the total serum cholesterol and the level of low        density lipoproteins (LDL);    -   increases in the level of uric acid which is linked to heart        disease;    -   increasing in the level of blood lactic acid which can lead to        metabolic acidosis and death,    -   causing the loss of important nutrients minerals such as        calcium, phosphorus, magnesium and zinc;    -   increasing amounts of fat production; and    -   reducing the affinity of insulin for its receptor so that the        pancreas is actually induced to produce more insulin that it        would need for the same amount of glucose.

Energy dense and low GI foods are recommended for those at risk ofdiabetes and coronary heart disease. In light of these concerns, thereis a need for a low GI sweetener with fewer disadvantages. Sucroseproducts or sweeteners with low GI index are therefore desirable. Thereis thus a need for sugar to have its GI reduced so that it is in the lowGI range (54 or less) and more acceptable for a low GI diet.

BRIEF SUMMARY OF THE DISCLOSURE

It has now been found that the final waste streams and some in-processproducts in the sugar manufacturing process contain useful substanceswhich can be used to modify the energy density, burn rate and GI ofsugar products and food containing sugar.

According to a first aspect of the invention, there is provided amolasses extract having GI or burn rate reducing characteristicscomprising substantially no content of any carbohydrates having GIincreasing characteristics.

The molasses extract may contain one or more of the followingsubstances: lipids, phospholipids, protein, flavonoids such asanthocyanins, catechins, chalcones, flavonols and flavones, polyphenols,antioxidants, phytosterols such as 1-octacosanol, campesterol,stigmasterol, β-sitosterol, oligosaccharides such as raffinose,1-kestose, theanderose, 6-kestose, panose, neo-kestose and nystose, andorganic acids such as c-aconitic acid, citric acid, phosphoric acid,gluconic acid, malic acid, t-aconitic acid, succinic acid and lacticacid, aliphatic alcohols, vitamins, minerals, carbohydrates, gums andneutral and polar lipids.

A person skilled in the art will know what carbohydrates have GIincreasing characteristics. Typical examples of carbohydrates having GIincreasing characteristics are sucrose, glucose, simple polysaccharidesand pectins.

According to a second aspect of the invention, there is provided a sugarmud extract having GI or burn rate reducing characteristics comprisingsubstantially no content of any carbohydrates having GI increasingcharacteristics.

The sugar mud extract may contain one or more of the followingsubstances: lipids, phospholipids, protein, flavonoids such asanthocyanins, catechins, chalcones, flavonols and flavones, polyphenols,antioxidants, phytosterols such as 1-octacosanol, campesterol,stigmasterol, β-sitosterol, oligosaccharides such as raffinose,1-kestose, theanderose, 6-kestose, panose, neo-kestose and nystose, andorganic acids such as c-aconitic acid, citric acid, phosphoric acid,gluconic acid, malic acid, t-aconitic acid, succinic acid and lacticacid, aliphatic alcohols, vitamins, minerals, carbohydrates, gums andneutral and polar lipids.

According to a third aspect of the invention, there is provided anextract from the juice and/or foam collected from the clarifying tankhaving GI or burn rate reducing characteristics comprising substantiallyno content of any carbohydrates having GI increasing characteristics.

The clarifying tank extract may contain one or more of the followingsubstances: lipids, phospholipids, protein, flavonoids such asanthocyanins, catechins, chalcones, flavonols and flavones, polyphenols,antioxidants, phytosterols such as 1-octacosanol, campesterol,stigmasterol, β-sitosterol, oligosaccharides such as raffnose,1-kestose, theanderose, 6-kestose, panose, neo-kestose and nystose, andorganic acids such as c-aconitic acid, citric acid, phosphoric acid,gluconic acid, malic acid, t-aconitic acid, succinic acid and lacticacid, aliphatic alcohols, vitamins, minerals, carbohydrates, gums andneutral and polar lipids.

According to a fourth aspect of the invention, there is provided anextract from sugar cane or sugar beet field trash/fibrated sugar canetops having GI or burn rate reducing characteristics comprisingsubstantially no content of any carbohydrates having GI increasingcharacteristics.

The sugar cane or sugar beet field trash/fibrated sugar cane topsextract may contain one or more of the following substances: lipids,phospholipids, protein, flavonoids such as anthocyanins, catechins,chalcones, flavonols and flavones, polyphenols, antioxidants,phytosterols such as 1-octacosanol, campesterol, stigmasterol,β-sitosterol, oligosaccharides such as raffinose, 1-kestose,theanderose, 6-kestose, panose, neo-kestose and nystose, and organicacids such as c-aconitic acid, citric acid, phosphoric acid, gluconicacid, malic acid, t-aconitic acid, succinic acid and lactic acid,aliphatic alcohols, vitamins, minerals, carbohydrates, gums and neutraland polar lipids.

According to a fifth aspect of the invention, there is provided anextract from bagasse/pulp having GI or burn rate reducingcharacteristics comprising substantially no content of any carbohydrateshaving GI increasing characteristics.

The bagasse/pulp extract may contain one or more of the followingsubstances: lipids, phospholipids, protein, flavonoids such asanthocyanins, catechins, chalcones, flavonols and flavones, polyphenols,antioxidants, phytosterols such as 1-octacosanol, campesterol,stigmasterol, β-sitosterol, oligosaccharides such as raffinose,1-kestose, theanderose, 6-kestose, panose, neo-kestose and nystose, andorganic acids such as c-aconitic acid, citric acid, phosphoric acid,gluconic acid, malic acid, t-aconitic acid, succinic acid and lacticacid, aliphatic alcohols, vitamins, minerals, carbohydrates, gums andneutral and polar lipids.

As used herein, the term “molasses” refers to the dark syrup which isleft behind after the bulk sugar crystals are collected in the sugarcane mill, the black syrup remaining after the sugar cane syrup has beencentrifuged for the last time in the refinery or beet molasses.Preferably, the molasses used is from the sugar cane mill.

As used herein, the term “sugar mud” refers to the dense substancecollected as waste during the clarification of the sugar cane juice inthe sugar cane mill or the calcium carbonate mixture collected duringclarification of sugar beet juice.

As used herein, the term “juice or foam from the clarifying tank” refersto the in-process product comprising the lighter substances collectedduring the clarification of the sugar cane juice in the sugar cane mill.

As used herein, the term “field trash/fibrated sugar cane tops” refersto the material collected as waste after harvesting. In particular,field trash refers to waste from harvesting either sugar cane or sugarbeets.

As used herein, the term “bagasse” refers to the left over fibrousmaterial after the raw sugar cane juice has been extracted. As usedherein, the term “pulp” refers to the material left after the sugar beetjuice has been collected.

As used herein, the term “in-process products” in the sugarmanufacturing process refers to stages of the sugar refining processwhere the product is substantially less refined. For example, the juiceor foam from the clarifying tank and the sugar syrup obtained from thesugar beets are in-process products.

As used herein, “substantially no content of any carbohydrates having GIincreasing characteristics” refers to a composition wherein the amountof GI increasing carbohydrates does not inhibit the GI lowering effectsof the extract. A person skilled in the art will know that if theextract contains more GI increasing carbohydrates then the extract willneed to contain more GI lowering components. Preferably, the extract hasno more than 2% of GI increasing carbohydrates. More preferably, thereis no more than 1.5%.

According to a sixth aspect of the invention, there is provided a methodfor extracting non-nutrient phytochemicals having GI or burn ratereducing properties from sugar processing waste streams and otherin-process products such as juice or foam from the clarifying tank,molasses, mill mud, pulp and bagasse the method comprising the followingsteps:

-   -   extracting non-nutrient phytochemicals from the sugar processing        waste streams and other in-process products using an aqueous        solvent;    -   filtering the extracted non-nutrient phytochemicals to remove        particulate matter;    -   separating the low and high molecular weight components by size        exclusion processing using either gel permeation chromatography        or ultrafiltration;    -   optionally, separating the low and high molecular weight        components using ion exchange and/or a combination of        hydrophobic chromatography; and    -   recovering the extracted non-nutrient phytochemicals.

Pure fractions of components are recovered and can be concentrated bymicrofiltration, reverse osmosis, vacuum evaporation and freeze drying.

The small molecular weight components include, but are not limited to,mono and disaccharides, anions, cations, organic and amino acids, andpeptides. The large molecular weight components include, but are notlimited to, oligo and polysaccharides, proteins, polyphenols and otherphytochemicals.

In another embodiment, the method for extracting non-nutrientphytochemicals having GI or burn rate reducing properties from sugarprocessing waste streams and other in-process products such as juice orfoam from the clarifying tank, molasses, mill mud, and bagasse themethod comprising the following steps:

-   -   extracting non-nutrient phytochemicals from the sugar processing        waste streams and other in-process products using an aqueous        solvent;    -   filtering the extracted non-nutrient phytochemicals to remove        particulate matter;    -   separating the low and high molecular weight components using        ion exchange chromatography with fractions eluted from the resin        by a stepwise increase in pH;    -   further treating the fractions and unabsorbed material using ion        exchange;    -   further treating the fractions and unabsorbed material by size        exclusion processing using either gel permeation chromatography        or ultrafiltration and/or hydrophobic chromatography; and    -   recovering the extracted non-nutrient phytochemicals.

Pure fractions of components are recovered and concentrated by acombination of microfiltration, reverse osmosis, vacuum evaporation andfreeze drying.

According to a seventh aspect of the invention, there is provided amethod for extracting non-nutrient phytochemicals having GI or burn ratereducing properties from sugar cane mill mud, the method comprising thefollowing steps:

-   -   drying the mill mud;    -   extracting the dried material using an aqueous or organic        solvent;    -   repeating the extraction followed by solvent fractionation and        partitioning as required; and    -   drying the extracted material.

According to an eighth aspect of the invention, there is provided amethod for lowering the GI of a food product, the method comprisingcombining the food product with an effective amount of a GI or burn ratelowering extract selected from the first, second, third, fourth or fifthaspects of the invention and mixtures thereof.

Preferably, the food product is a sucrose-containing product or similar.This may include an in-process product stream.

Preferably, the ratio of extract to food product is in the range from1:10 to 1:0.5. More preferably, the ratio of extract to food product isin the range from 1:5 to 1:2.5. Most preferably, the ratio is 1:2.5.

Preferably, the GI or burn rate lowering extract further comprisesnutrients. A person skilled in the art will know that the over refiningof foods and therefore their metabolism can lead to a loss of nutrients,therefore it is useful for the food product to also replace thosenutrients. Typically, such nutrients would comprise vitamins, minerals,proteins and other carbohydrates including complexes.

Preferably, the method further comprises combining the food product withphytochemicals not derived from sugarcane. The phytochemicals mayinclude nutrients or non-nutrients.

Preferably, the phytochemicals are selected from the group consisting ofvitamins, minerals, lipids, protein, flavonoids, polyphenols,pre-biotics, monosaccharides, disaccharides, fructo-oligosaccharides(inulins), oligosaccharides, gums, thickeners (including but not limitedto pectins, amylopectins, arabinose, starches, such as Hi-maize etc),galactose, galacto-oligosaccharides, and other carbohydrates havingproperties likely to improve bowel health and function, modifyviscosity, further lower GI, slow burn rate or otherwise modify enzymedigestion, reduce insulinaemic response and/or change energy density.

According to a ninth aspect of the invention, there is provided asucrose-containing product comprising:

-   -   (a) a sucrose-containing product; and    -   (b) an effective amount of a GI or burn rate lowering extract        selected from the first, second, third or fourth aspects of the        invention and mixtures thereof.

Preferably the sucrose-containing product is a highly refined product.

According to a tenth aspect of the invention, there is provided asucrose-containing product having a GI no greater than 54.

As used herein “sucrose-containing products” include but are not limitedto crystals, syrups, granules, blends and milled powders derived fromsugar cane or sugar beet. It further includes any product from the sugarmanufacturing process after first expressed juice or the first extractof molasses has been removed.

According to an eleventh aspect of the invention, there is provided amethod for producing food products having a lower GI or burn rate, themethod comprising replacing the sweetener previously used in the foodproduct with a sucrose-containing product which has been combined withan effective amount of a GI or burn rate lowering extract selected fromthe first, second, third or fourth aspects of the invention and mixturesthereof.

According to a twelfth aspect of the invention, there is provided amethod for improving health comprising administering an effective amountof a GI or burn rate lowering extract selected from the first, second,third, fourth or fifth aspects of the invention and mixtures thereof.

Preferably, the method further comprises combining the GI or burn ratelowering extract with a sweetener.

According to a thirteenth aspect of the invention, there is provided amethod for lowering the GI of a sucrose-containing product, the methodcomprising combining the sucrose-containing product with bioactivecompounds not derived from sugarcane having GI lowering propertiesaccording to this invention. For example such sources of these bioactivecompounds may include extracts of algae, yeasts, moulds, bacteria andfrom other genera within the Gramineae family, and Theobroma genera. Thebioactive compounds may include nutrients and non-nutrients. Preferably,the bioactive compounds are selected from the group consisting ofpolyphenols, flavonoids, antioxidants, pre-biotics, monosaccharides,disaccharides, fructo-oligosaccharides (inulins), oligosaccharides,galactose, galacto-oligosaccharides, vitamins, minerals, lipids,protein, gums, thickeners (including but not limited to pectins,amylopectins, arabinose, starches, Hi-maize etc), and othercarbohydrates having properties likely to improve bowel health andfunction, lower GI, slow burn rate, reduce insulinaemic response and/orchange energy density or which bind and inhibit enzymes such asamylases, glucosidases, peptidases and proteases to reduce digestion andhence glucose release into the bloodstream.

According to a fourteenth aspect of the invention, there is provided aproduct having a low GI comprising:

-   -   sugar cane molasses;    -   a palate-improving amount of a sweetener including, but not        limited to, sucrose and fructose, and    -   GI Lowering Carbohydrates.

Typically, the GI lowering carbohydrates are selected from the groupconsisting of pre-biotics, monosaccharides, disaccharides,fructo-oligosaccharides, oligosaccharides, galactose,galacto-oligosaccharides, gums, thickeners (including but not limited topectins, amylopectins, arabinose, starches, Hi-maize etc), flavonoidsand other carbohydrates having properties likely to improve bowel healthand function, lower GI, slow burn rate, reduce insulinaemic responseand/or change energy density or which bind and inhibit enzymes such asamylases, glucosidases, peptidases and proteases to reduce digestion andhence glucose release into the bloodstream.

According to a fifteenth aspect of the invention, there is provided apurified phytochemical extracted from sugar cane or sugar beet which hasGI lowering properties. Preferably, the purified phytochemical comprisesone or more of the following: lipids, phospholipids, protein, flavonoidssuch as anthocyanins, catechins, chalcones, flavonols and flavones,polyphenols, antioxidants, phytosterols such as 1-octacosanol,campesterol, stigmasterol, β-sitosterol, oligosaccharides such asraffinose, 1-kestose, theanderose, 6-kestose, panose, neo-kestose andnystose, and organic acids such as c-aconitic acid, citric acid,phosphoric acid, gluconic acid, malic acid, t-aconitic acid, succinicacid and lactic acid, aliphatic alcohols, vitamins, minerals,carbohydrates, gums and neutral and polar lipids.

In a preferred embodiment, there is provided a method for lowering theGI of sucrose-containing products, the method comprising combining thesucrose-containing product with a purified phytochemical extracted fromsugar cane or sugar beet which has GI lowering properties.

In a further embodiment, there is provided a method for lowering the GIof food products, the method comprising combining the food product witha purified phytochemical extracted from sugar cane which has GI loweringproperties.

According to a sixteenth aspect of the invention, there is provided asweetener having a low GI comprising

-   -   a sugar base comprising 97% to 99% of a mixture consisting of        sucrose, glucose and fructose wherein preferably the combined        amount of glucose and fructose is no more than 0.5% w/w of the        total sweetener,    -   one or more organic acids selected from the group consisting of        trans-aconitic acid, oxalic, cis-aconitic, citric, phosphoric,        gluconic, malic, succinic, lactic, formic and acetic acids,        wherein preferably the total amount of acids in the sweetener is        an amount in the range from 600 to 2100 micrograms per gram, and        wherein preferably the amount of trans-acotinic acid forms the        majority of the organic acids and is in an amount in the range        from 200 to 600 micrograms per gram;    -   one or more minerals, preferably selected from the group        consisting of calcium, magnesium and potassium, wherein        preferably the amount of minerals is in the range from 150 to        600 micrograms per gram, and wherein preferably the ratio of        calcium to magnesium to potassium is 50:15:35;    -   one or more polyphenols preferably in an amount in the range        from 0.2 to 0.5 mg catechin equivalents per gram;    -   one or more antioxidants wherein preferably the antioxidant        activity is in the range of 0.4 to 1.2 micromoles per gram; and    -   one or more polysaccharides, preferably in the range from 20 to        60 micrograms per gram.

The preferred embodiment according to this aspect of the inventionprovides a low GI sweetener without compromising on the taste orfunctionality of normal table sugar. Preferably the organic acids,minerals, polyphenols, antioxidants and polysaccharides are provided inan extract from sugar cane or sugar beets.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 shows a chromatogram of the extract (after derivation) from sugarcane tops.

FIG. 2( a) shows a chromatogram of the extract (after derivatisation)from sugar cane bagasse.

FIG. 2( b) shows an expanded section of the chromatogram of the extract(after derivatisation) from sugar cane bagasse.

FIG. 3( a) shows a chromatogram of the extract (after derivatisation)from sugar cane mill mud.

FIG. 3( b) shows an expanded section of the chromatogram of the extract(after derivatisation) from sugar cane mill mud.

FIG. 4 shows a polar lipid profile extracted from sugar cane.

FIG. 5 is the ESMS trace for the bound extracted components from Example3.

FIG. 6 is the ESMS trace for the unbound extracted components fromExample 3.

FIG. 7 is the ESMS trace for the crude sugar cane molasses startingmaterial used in Example 3.

FIG. 8 is the HPLC trace for the extracted material from Example 3.

FIG. 9 is the HPLC trace for the crude sugar cane molasses startingmaterial used in Example 3.

FIG. 10 is a plot of the pH for the different formulations in Example10.

FIG. 11 is a flow chart discussed herein.

FIG. 12 is a flow chart discussed herein.

DETAILED DESCRIPTION

Naturally derived refined sweeteners with added non-nutrientphytochemicals and nutrients are not known in the market. Sugar cane andsugar beet contain many non-nutrient phytochemicals including, but notlimited to, aliphatic alcohols, organic acids, phospholipids,flavonoids, polyphenols and sterols. Each of the sugar processing wastestreams and other in-process products such as juice or foam from theclarifying tank, molasses, mill mud, pulp and bagasse may contain adiverse range of these non-nutrient phytochemicals including solublegums, phytosterols, waxes and phospholipids.

The present invention relates to the production of natural sugar caneand sugar beet sweeteners which have a different energy density, lowerGI and slower burn rate compared to currently available highly refinedsucrose products. The natural sugar cane and sugar beet sweetenersaccording to the invention can be produced by adding extracts of currentproduction waste streams and in-process products or other carbohydratesto the currently available highly refined sucrose products.

Alternatively the natural sugar cane and sugar beet sweeteners accordingto the invention can be produced by redirecting these waste streams bychanges in the current process, or by returning extracts of these wastestreams back into the manufacturing process to incorporate thesecompounds in or on the sugarcane sweetener. The extracts from thecurrent production waste streams add soluble gums, fibres, hydrolysedcelluloses and other slowly digested carbohydrates to the sucroseproduct and thus lower the GI of the product and promote health.Associated health benefits include, but are not limited, to lowering therisk of diabetes and coronary heart disease.

The method for extracting the sugar cane or sugar beet nutrients andphytochemicals incorporates taking the first, second and third extractsof molasses and or sugar syrup or other molasses products, field trash,growing tips, mill mud, pulp, bagasse and in process products subjectingthose extracts to fractionation, and thereafter adding these extractsback into the high purity sucrose product. Preferably, the molasses,field trash, growing tips, mill mud, bagasse and in-process products aretaken from the sugar cane mill. The method may also include takingextracts of the first second and third extracts of molasses or cane orbeet molasses products, then adding one or all of these fractions backinto the high purity sucrose product. In one embodiment, a mix of one ormore sugar phytochemicals are extracted from molasses then blended backinto sucrose products.

These phytochemicals are valuable compounds and capable of promotinghealth when added back in higher concentration than usually found insugar.

The method provides a means for preserving phytochemical levelsoccurring in the sugarcane or sugar beet feedstock in the finalproducts. In another embodiment this is achieved by adding back one ormore of the first, second and or the third cuts of molasses from thesugar refining processes. In another embodiment, phytochemicals from oneor more of the cuts are extracted then added back to the sucroseproduct.

In another embodiment phytochemicals are extracted from sugar processingwaste streams and other in-process products such as juice or foam fromthe clarifying tank, molasses, mill mud, and bagasse then added backinto the high purity sucrose product. Various solvents can be used toextract the phytochemicals. Such food grade solvents are known in theart of phytochemical extraction including but not limited to variouspolar and non-polar solvents, such as alcohols. In another embodimentphytochemicals are extracted from field trash then added back to thesucrose product.

The mix of phytochemicals which is extracted from the molasses, fieldtrash, growing tips, mill mud, pulp, bagasse and in process products isadded to the sucrose products to lower GI of the finished product. Inaddition to having a lower GI, the natural sweetener has a slower burnrate providing sustained energy.

Sugar cane and sugar beet “non-nutrient phytochemicals” include but arenot limited to flavonoids (8 subgroups: Flavonols (eg quercetin,kaempferol, myricetin andisorhanmetin); Flavones (eg luteolin, tricinand apigenin); Flavanones (eg hesperetin, naringenin anderiodictyol);Flavan-3-ols (eg catechin, gallocatechin, epicatechin, epigallocatechin,epicatechin 3-gallate, epigallocatechin 3-gallate and theaflavin);Anthocyanidins (eg cyanidin, delphinidin, malvidin, pelargonidin,peonidin and petunidin); Anthocyanosides: Curcuminoids; andProanthocyanins) and their derivatives, including but not limited to,natural and synthetic conjugates such as glycosides, glucosides,galactosides, galacturonides, ethers, esters, arabinosides, sulphates,phosphates; aldopentoses (xylose, arabinose) aldohexoses (mannose),ketopentoses, ketohexoses (fructose), kestoses, soluble gums, aliphaticalcohols (and complexes), waxes (and complexes), polysaccharides,oligosaccharides, non-nitrogenous compounds (organic acids), minerals,mineral complexes (organic iron and other minerals), phytochemicalcomplexes (including but not limited to glucosides, glycosides,glycosylates, esters, glucopyranosides etc), chlorophyll, phytosterols(and complexes), phytostanols (and complexes), hydrolysed celluloses andphospholipids. It is anticipated that the range or mix of non-nutrientphytochemicals can be changed during extraction by using varioussolvents, extraction conditions and methods. This includes but is notlimited to conversion to and production of more amino sugars(glucosamine, mannosamine) and subsequent polymeric forms. Furthermore,it is also envisaged that this invention also includes syntheticderivatives, including, but not limited to, the above.

In a preferred embodiment, the extract from the molasses, field trash,growing tips, mill mud, pulp, bagasse and in process products willfurther comprise nutrients such as monosaccharides, aldotetroses,nitrogenous compounds (proteins, amino acids) and vitamins (biotin,choline, folic acid, niacin, pantothenic acid, riboflavin, pyridoxine,thiamine) and polyphenols (and complexes).

Without wishing to be bound by theory, certain classes of phenols,flavonoids and polyphenols or the like are reported to bind and inhibitenzymes such as amylases, glucosidases, peptidases and proteases toreduce digestion and hence glucose release into the bloodstream.

As used herein, the term “food” or “food product” includes any edibleproduct, such as but not limited to confectioneries, supplements, snacks(sweet and savory), cocoa-containing foods, flavors, beverages, dietarysupplements and formulations including supplements used in animal healthand nutrition. Confectioneries refer to any sweetened foods, includingbut not limited to candy, chocolate, chewing gum icings, fruit pulpbased delivery systems and the like. Additional ingredients desired inthe resulting food product may be added at any point in the process.Food products may also encompass for example, complex confections wherechocolate is combined with and generally coats other foods such ascaramels, nougat, fruit pieces, nuts, wafers, biscuits, ice cream or thelike.

The natural sweeteners formed according to the invention can be usedalone, in combination or added into foods to improve the functionalbenefits associated with such foods.

The following tables demonstrate the components in sugar beet wasteproducts.

Typical Analysis of Beet Pulp Pellets Component Dry As Fed Dry Matter100.00 91.50%  Moisture 0.00  8.5% Protein, Crude 9.21 8.42% TDN 74.0867.78%  ADF—Acid Detergent Fiber 22.71 20.78%  NEL—Net Energy Lactation77.04 70.49 Mcal/lb NEG—Net Energy Gain 51.79 47.38 Mcal/lb NEM—NetEnergy Maintenance 80.00 73.20 Mcal/lb TDN—Total Digestible Nutrients74.08 67.78%  Fat (Ether Extract) 0.70 0.64% Ash 6.22 5.69% Crude Fiber18.17 16.62%  Calcium 1.72 1.57% Phosphorus 0.08 0.073%  Potassium 0.360.33% Sulfur 0.38 0.35% Total Sugars 9.56 8.75% Boron 45.00 41.17 ppmManganese 86.00 78.70 ppm Zinc 21.00 19.21 ppm Copper 16.00 14.64 ppmIron 308.00 281.82 ppm Aluminum 259.00 236.98 ppm Sodium 911.00 833.56ppm

Typical Analysis of Beet Molasses Component Dry Basis As Fed Dry Matter78.70%  Moisture 21.30% Protein, Crude 11.65 8.51% Fiber, Crude 0.140.11% ADF—Acid Detergent Fiber 0.0  0.0% NEL—Net Energy Lactation 0.900.71 Mcal/lb NEG—Net Energy Gain 0.67 0.53 Mcal/lb NEM—Net EnergyMaintenance 1.00 0.78 Mcal/lb TDN—Total Digestible Nutrients 85.6567.45%  Fat 0.34 0.30% Ash 10.46 8.40% NEF—Nitrogen Free Extract 75.9363.40%  Calcium 0.12 0.09% Phosphorus 0.08 0.06% Potassium 4.38 3.66% PH7.25 s.u. Reducing Sugars 2.78% TSI—Total Sugars as Invert 54.20%  Brix83.40 s.u.

EXAMPLES

The invention will now be further explained and illustrated by referenceto the following non-limiting examples.

Example 1

In this example, adding a molasses extract having GI or burn ratereducing properties according to the invention into a high puritysucrose product produced a natural sweetener. The phytochemical extractwas produced using polar and non-polar solvent countercurrent extractionprocedures. Other procedures known in the art including specific ionexchange or gel exclusion chromatography can also be used.

A straight “A” massecuite was boiled to a 90% purity using pure canesyrup. The massecuite footing could be either a washed high purity magmaor high grade graining. Once the massecuite reached the appropriatedegree of supersaturation it was fugalled to produce a sugar crystal ofapproximately 99.6% purity. Prior to crystals exiting the dryer, a mixof phytochemicals extracted from the first, second and third molassesextracts was sprayed onto the surface of the crystal. Resulting crystalshad a higher content of natural phytochemicals. The crystals can beground to desired particle size. The finished product is a free flowingdarker crystalline mix that is dispersible in water and can be baggedand sold on the wholesale or retail markets.

Example 2

This example investigated the presence of aliphatic alcohols(policosanols) and phytosterols in fibrated sugar cane tops, bagasse andmill mud.

Extraction and Derivatisation Procedures

-   -   Fibrated cane tops were dried in a vacuum oven at 40° C. for one        week. The dried material (9.58 g) was exhaustively extracted        with n-heptane (boiling point 98° C.) using a soxhlet extractor        for about four hours during which time at least 10 cycles were        completed. The extract was dried over anhydrous sodium sulphate        and evaporated to dryness to give 115 mg of oily/waxy material        (1.2% yield, based on dry weight of cane tops).    -   Bagasse was treated in the same manner. The dried material        (7.60 g) gave 50 mg of oily/waxy material (0.65% yield, based on        dry weight of bagasse).    -   Mill mud was treated in the same manner. The dried material        (9.92 g) gave 650 mg of oily/waxy material (6.53% yield, based        on dry weight of mill mud).

All three extracts were saponified after melting at 80-100° C. in thepresence of sodium hydroxide (5 mL, 10M solution) and heating at 95° C.for 2.5 hours. n-Heptane (5 mL, containing dihydrocholesterol asinternal standard, 0.98 mg) was added to give a 2-phase system and themixture was heated for a further two hours to ensure that thesaponification was complete. In the case of the mill mud extract, asub-sample (128 mg) was taken because of the greater quantity of thismaterial.

The sodium hydroxide layer was removed and the organic layer washed withthree lots of water. The n-heptane extract was evaporated to dryness andthen extracted with boiling 95% ethanol (4×10 mL). The combined ethanolextracts were evaporated to dryness, dissolved in dry pyridine (1 mL)and N-methyl-N-trimethylsilylacetamide (2 mL) was added. The tubescontaining the mixtures and a small teflon stirring bar were flushedwith nitrogen and sealed. The mixtures were heated at 70° C. withstirring for one hour. A small volume (six drops of the cane tops andbagasse extracts and three drops of the mill mud extract) wastransferred to glass vials (2 mL) and n-heptane (about 2 mL) was added.The mixtures were analysed by Gas Chromatography/Mass Spectrometry(GC/MS). A calibration mixture of dihydrocholesterol (1.50 mg),n-octacosanol (2.02 mg) and 3-sitosterol (1.25 mg) was treated in thesame manner. Dihydrocholesterol was chosen as the internal standardbecause this compound could be obtained with high purity, it is morechemically stable than most sterols (which often having one or severaldouble bonds) and it was well-separated on the HP 5-MS column from thetargeted components. In addition, the major high mass fragments weredifferent from those of the targeted components.

GC/MS Analysis

The GC/MS analyses were performed using a HP 5890N gas chromatograph(split/splitless) with a HP 5973N mass selective detector and a GerstelMPS autosampler system. The capillary column, elution conditions anddetection conditions are shown in table 1. The HP 5-MS capillary coatingis polydimethylsiloxane with 5% phenyl substituents.

Instrumental conditions for the GC/MS investigation of natural products.Gas chromatography HP 5890 (Agilent, Palo Alto, USA) GC column HP 5-MS(length 30 m, inner diameter 0.25 mm, film thickness 0.25 μm) Carriergas He, 16.53 psi Injector temperature 260° C. Oven temperature 100° C.to 300° C. Temperature program 10° C./min Mass spectrometry HP 5973N(Agilent, Palo Alto, USA) Ionization energy 70 eV Interface temperature260° C. Scanning range 35 amu to 555 amu

Results and Discussion

The chromatograms of the three extracts after derivatisation are shownin FIGS. 1-3.

(Note: the components shown in the chromatogram are primarilytrimethylsilyl derivatives.)

The removal of the sodium hydroxide solution following saponificationresulted in the removal of acidic components and more water-solublecompounds from the materials that subsequently were analysed. Thesecompounds included phenolic compounds known to be present in caneproducts. Other approaches are needed to analyse for these components.The extraction of materials with ethanol provided a separation of thenon-polar components such as alkanes from the more polar components thatincluded the alcohols and sterols (the materials in the extractsanalysed), although these compounds are only marginally more polar.

The yield of individual components on the basis of dry weight of canematerial or mill mud was recorded rather than on the basis of weight ofextractive because the conditions of extraction and processing of thecrude waxes in an industrial process will affect the yield of eachcomponent.

The compounds were converted to their trimethylsilyl derivatives so thatthey could be analysed by GC/MS. All determinations were based on peakarea of components. The determination of campesterol and stigmasterolwas based on the assumption that their response factors were similar to3-sitosterol. This seems reasonable because of the overall similarity ofthe mass spectra of all three sterols, and it is the abundance of ionsand pattern that determine the peak areas of the different components.

The relative proportions of alcohols were determined from their peakareas but when occurring as very small peaks (as most were), there isthe greater likelihood of other co-eluting components leading to anoverestimation of their concentration. A more accurate estimation can bemade on the basis of the peak areas of the base peak in the massspectrum, i.e. the [M−15]+ion fragment, where M is the molecular weight.

The content of n-octacosanol and the three major sterols in the canetops, bagasse and mill mud are shown in Tables 1-3.

TABLE 1 Content of n-octacosanol and sterols in cane tops Retention time(min) Compound Content (mg/kg of dried material) 39.98 n-octacosanol 19841.45 Campesterol 210 41.84 Stigmasterol 140 42.54 β-Sitosterol 590Total (3 sterols) 940

TABLE 2 Content of n-octacosanol and sterols in bagasse Retention time(min) Compound Content (mg/kg of dried material) 39.98 n-octacosanol 6741.45 Campesterol 100 41.84 Stigmasterol 65 42.54 β-Sitosterol 300 Total(3 sterols) 463

TABLE 3 Content of n-octacosanol and sterols in mill mud Retention time(min) Compound Content (g/kg of dried material) 39.99 n-octacosanol 2.6141.45 Campesterol 1.30 41.84 Stigmasterol 1.34 42.54 β-Sitosterol 2.89Total (3 sterols) 5.52

The cane tops gave a higher yield (about 2-fold) of these compoundscompared with bagasse but the mill mud provided the richest yield. Smallquantities of compounds having mass spectra indicative of sterols weredetected in the mill mud extract. These components with retention timesof 42.78, 42.92 and 43.23 minutes amounted to only about 3% (each) ofthe β-sitosterol content and no attempt was made to identify them.Whilst n-octacosanol was the major component in the group of alcoholspresent, small quantities of even carbon chain homologues were alsodetected (see earlier) along with the closely related odd carbon chainhomologues-see tables. The content of alcohols in the cane tops, bagasseand mill mud are shown in Tables 4-6.

TABLE 4 Alcohols in cane tops Retention time Number of Content (mg/kg ofdry (min) Compound carbon atoms material) 21.85 n-Tetradecanol 14 423.47 n-Hexadecanol 16 8 25.47 n-Octadecanol 18 18 28.80 n-Eicosanol 207 31.89 n-Docosanol 22 2 34.77 n-Tetracosanol 24 n.d.* 37.45n-Hexacosanol 26 18 38.66 n-Heptacosanol 27 2 40.27 n-Octacosanol 28 19841.12 n-Nonacosanol 29 15 42.36 n-Triacontanol 30 38 45.18n-Dotriacontanol 32 n.d. *n.d. less than 1 mg/kg of dry material

TABLE 5 Alcohols in bagasse Retention time Number of Content (mg/kg ofdry (min) Compound carbon atoms material) 21.85 n-Tetradecanol 14 223.47 n-Hexadecanol 16 1 25.47 n-Octadecanol 18 1 28.80 n-Eicosanol 20n.d.* 31.89 n-Docosanol 22 4 34.77 n-Tetracosanol 24 1 37.45n-Hexacosanol 26 3 38.72 n-Heptacosanol 27 n.d. 40.28 n-Octacosanol 2867  41.12 n-Nonacosanol 29 5 42.37 n-Triacontanol 30 7 45.18n-Dotriacontanol 32 n.d. *n.d. less than 1 mg/kg

TABLE 6 Alcohols in mill mud Retention time Number of Content (mg/kg ofdry (min) Compound carbon atoms material) 21.83 n-Tetradecanol 14 0.0123.47 n-Hexadecanol 16 0.84 25.47 n-Octadecanol 18 n.d.* 28.80n-Eicosanol 20 n.d. 31.88 n-Docosanol 22 0.01 34.77 n-Tetracosanol 240.02 37.46 n-Hexacosanol 26 0.37 38.73 n-Heptacosanol 27 0.03 39.99n-Octacosanol 28 2.61 41.12 n-Nonacosanol 29 0.28 42.36 n-Triacontanol30 0.28 45.18 n-Dotriacontanol 32 0.19 *n.d. less than 0.01 g/kg

Discussion

The major components present in the extracts of all three sugar canederived materials were long-chain alcohols and sterols. The majoralcohol was n-octacosanol, which occurred with smaller quantities ofother closely-related alcohols with those having an even number ofcarbon atoms dominating. The major sterols were campesterol,stigmasterol and β-sitosterol but minor quantities of other sterols alsowere present, based on mass spectral data.

Example 3 Method for Molasses Fractionation

The flowchart shown in FIG. 12 illustrates the process used to extractthe GI lowering phytochemicals from sugar cane molasses.

The following analysis was completed.

Electrospray Mass Spectrometry (ES/MS) was conducted on a MicromassPlatform ES/MS. The samples were dissolved in Methanol/Water (80:20) andinjected into a 20 μl loop and eluted with methanol/water (80:20) at 20μl/min. MS analysis was conducted in negative ion mode with a conevoltage of 40 kV and a mass range of 50-700 Da. FIGS. 5 to 7 show theresultant traces.

High Pressure Liquid Chromatography (HPLC) was conducted using a Waters600 with auto-injector. The column was a Keystone ScientificODS-Hypersil (150×4.6 mm). The sample was dissolved in 50%acetonitrile/water and 10 μl was injected. The sample was eluted withacetonitrile/20 mmol acetic acid (15:85) at 1 ml/min. The sample wasdetected at 210-400 nm with an extracted wavelength of 220 nm. FIGS. 8and 9 show the resultant traces.

Discussion

The traces show that the low GI extract (bound material) consistedmostly of low molecular weight polyphenols with the sucrose, fructoseand glucose removed.

Example 4

This example investigated the content of lipids and proteins in sugarcane waste streams to assist with understanding the GI loweringproperties of extracts from molasses, bagasse, mill mud and fieldtrash/fibrated cane tops.

Methods

Lipid content from bagasse was determined by the method of Folch et al(1957). Phospholipid level was determined by the method of Ames andDubin (1960). Organic phosphorus was multiplied by 25 to give thephospholipid content. Total solids content was determined using theAustralian Standard Method AS2300.1.1. Total nitrogen levels weredetermined using the AOAC method AOAC (2000) 920.176. Total nitrogen wasmultiplied by 6.25 to give the protein content. Polyphenol content wasdetermined by a procedure based on that of Kim et al (2003) and usedcatechin as the standard. HPLC: The phospholipid profile of the lipidextract was obtained by normal phase HPLC using a Platinum silica columnwith a gradient elution system of trimethylpentane,iso-propanol/chloroform, and iso-propanol/water. Six peaks wereobtained, of which three were identified as phospholipids: phosphatidylserine; phosphatidyl ethanolamine; and lysophosphatidyl ethanolamine(see FIG. 4). These peaks accounted for approximately 15% of the totalpeak area. The remaining peaks were unidentified polar lipids, possiblyglycolipids, but this has not been confirmed. Neutral lipids were alsopresent, eluting immediately after the solvent peak (see FIG. 4).

Quantification of the phospholipid peaks indicated that 0.077 mg II/mglipid were present. This is lower than the value obtained by theprocedure of Ames and Dubin (above), 0.095 mg PL/mg lipid. It ispossible that other phospholipid components were masked by the largeunidentified peaks. Previous studies have shown good agreement betweenthese two procedures.

Results

TABLE 7 Lipid Phospholipid Total solids, Protein (%, m/m, (%, m/m, (%,m/m (TN × 6.25) Sample wet wt) wet wt) wet wt) (%, m/m, wet wt) Bagasse0.43 0.001 51.46 0.70 Clarifying 0.10 0.012 16.82 0.29 tank Mill mud0.44 0.061 26.19 0.09 (TN) Molasses 0.26 0.011 82.25 2.76

TABLE 8 Total Protein in Cane Samples Sample Protein (N × 6.25) (g/100g) First Expressed Juice 0.3 Final Juice <0.1 Syrup extracted from theclarified juice 0.5 Low pol Molasses 2.8 Mill Mud 2.0 Cane Tops Extract0.9

Discussion

Analysis of juice and foam from the clarifying tank detected surfactantsphosphatidyl serine, phosphatidyl ethanolamine and lysophosphatidylethanolamine. Although the foam sample had a low lipid content, a broadrange of neutral and unidentified polar lipids were detected (FIG. 4).In further analysis lipid, phospholipid and protein were detected in avariety of samples. Lipid was most concentrated in mill mud and bagasse.Bagasse was also a concentrated source of protein. With extractionsystems known in the art this fraction could be recovered. The mostconcentrated source of protein was surprisingly found in lowpol-molasses.

Example 5

This example investigated the antioxidant content of sugar cane wastestreams to assist with understanding the GI lowering properties ofextracts from molasses, bagasse, mill mud and field trash/fibrated canetops.

A catechin equivalent assessment of First Expressed juice, final juice,syrup, molasses, low pol sugar, mill mud, cane tops and foam wereundertaken.

Results

TABLE 9 Total Antioxidant Potential (*CE = catechin equivalents) Sample(mg CE*/mL) (mg CE*/g dry matter) First Expressed Juice 0.75 3.40 FinalJuice 0.12 8.76 Syrup extracted from the 2.89 3.43 clarified juiceMolasses 23.58  30.00 Low pol Sugar — 2.34 Filtrate 0.44 3.64 Cane tops0.44 13.54 Foam 0.23 3.75 Mill Mud — 3.17 High Pol Sugar 0.44 —

TABLE 10 Antioxidant potential of sugar cane extracts vs otherpolyphenol sources Polyphenols Antioxidants Sample (mg catechinequivs/g) (μmoles/g) Dark Chocolate 23.9 NT Milk Chocolate 7.25 18.3Cocoa liquor 41.8 110 Grape Seed Powder 301.5 1146 Grape Skin Extract54.5 181 Mixed Berry Snack 12.3 9.33 Mixed Juice 3.35 NT Mill mud 14.726.8 Molasses 17.87 32.58 High Pol sugar 0.25 0.44

Discussion

The analysis revealed that molasses was a surprisingly concentratedsource of antioxidants and similar to dark chocolate. In a purifiedform, it is likely that molasses antioxidants will be at least aseffective as antioxidants from other sources such as grape seed powder.These compounds are important to human health and can be utilized fortheir health promoting potential.

These compounds can be extracted then added back into sugarcane productsto lower GI and promote health.

Example 6

This example investigated the oligosaccharide, polysaccharide and othergum content of sugar cane waste streams to assist with understanding theGI lowering properties of extracts from molasses, bagasse, mill mud andfield trash/fibrated cane tops.

Results

TABLE 11 Total polysaccharide content of sugarcane processing and wastestreams Sample Total polysaccharide (mg/kg) FE Juice 7832 Final Juice38561 Syrup 5258 Low pol molasses 26610 Low pol sugar 3797 Cane TopsExtract 17063

Discussion

Final juice and low pol molasses were respectively the most concentratedpolysaccharide sources. On a dry weight basis low pol-molasses ishowever, the most concentrated. A crude extract of cane tops, molassesand final juice is used in sugarcane products to lower GI and improvehealth potential.

Example 7

This example investigated the acid content of sugar cane waste streamsto assist with understanding the GI lowering properties of extracts frommolasses, bagasse, mill mud and field trash/fibrated cane tops.

TABLE 12 Organic acid analysis by ICP-MS Organic: acid (ppm on drysolids) Samples Oxalic c-aconitic citric phosphoric Gluconic malict-aconitic succinic lactic formic acetic First Expressed Juice 221 6621091 2979 1310 1311 6157 132 36 23 485 Final Juice 778 1199 1258 452111678 1650 2811 395 0 0 4406 Syrup 217 320 1067 893 1568 1482 6616 324994 113 4723 Low pol Molasses 355 1177 749 726 1713 1057 10345 200 309119 1006 Low pol sugar 206 731 676 504 1203 786 3193 243 1348 203 3714Cane Tops extract 598 3043 2133 9235 7025 6938 49075 625 0 0 0 (solublesolids) Cane tops extract 81 413 290 1254 954 942 6665 85 0 0 0 (totalsolids)

Discussion

First Expressed juice, final juice, syrup, low pol molasses, low polsugar, and cane tops were assayed for organic acid content.Surprisingly, large quantities of many organic acids were detectedacross most of the samples analyzed. Cane tops and low pol molasses werethe most concentrated sources and lower GI or improve health potentialwhen conserved during processing or extracted then added back to sugarproducts.

Example 8

This example investigated the nutrient (cations, anions, vitamins andminerals) content of sugar cane waste streams to assist withunderstanding the GI lowering properties of extracts from molasses, millmud and field trash/fibrated cane tops.

Results

TABLE 13 Anion analysis by chromatography Anions (ppm on dry solids)Sample Fluoride Chloride Nitrite Bromide Nitrate Phosphate SulphateFirst Expressed Juice 186 3084 75 24 0 1277 2175 Final Juice 122 1738 0118 74 1637 1734 Syrup 133 3033 0 0 0 125 1834 Low pol Molasses 88522262 283 552 9 717 13279 Low pol sugar 187 2402 0 78 22 141 1173 MillMud 18 495 0 32 42 509 419 Cane Tops Extract 179 2668 0 5 2 680 3091Bagasse 10 153 2 0 3 160 196

TABLE 14 Cations identified by ICP-MS Element (ppm) Ca Fe K Mg Mn Na ZnSample Conc S.D. Conc. S.D. Conc. S.D. Conc S.D. Conc S.D. Conc S.D.Conc S.D. First Expressed 132 2 175 2 1260 12 164 1 15.9 0.1 14.1 0.12.40 0.06 Juice Final Juice <=0.05 15.2 0.2 15.0 21.4 7.59 0.15 1.060.03 0.227 0.003 <=0.05 Syrup 1280 19 12.7 0.7 4840 16 567 3 7.56 0.03125 1 0.891 0.025 Low pol Molasses 8444 13 120 2 25800 55 3860 10 54.40.4 2090 15 3.60 0.19 Low pol sugar 1120 12 12.3 0.1 3260 39 462 2 5.990.20 236 4 <=0.05 Cane Tops Extract 507 5 135 1 3970 34 418 3 20.0 0.16.08 0.15 11.0 0.1 Bagasse 290 8 162 2 224 11 176 1 14.9 0.2 19.0 0.1<=0.05

TABLE 15 Vitamins Ascorbic Acid Beta-Carotene Sample (mg/100 g) (ug/100g) First Expressed Juice <1 Not tested Final Juice <1 6.6 Low polMolasses <1 Not tested Low pol sugar <1 Not tested Mill Mud Not tested580 Cane Tops Extract <1 62

TABLE 16 Vitamins Pantothenic Niacin Acid Total (Vitamin B3) (VitaminB5) folates Vitamin K1 Sample (mg/100 g) (mg/100 g) (ug/100 g) (ug/100g) First Expressed <0.5 <1 <30 Not tested Juice Final Juice <0.5 <1 <30<10 Low pol 3.8 1.5 10 Not tested Molasses Low pol sugar 0.5 1 <30 Nottested Mill Mud Not tested Not tested Not tested <10 Cane Tops >0.5 1 20<10 Extract

TABLE 17 Mineral content by ICP-MS elemental analysis Results (Units -mg/Kg) Sample Ca Fe K Mg Mn Na Pb Zn Molasses C 5700 68.30 27400.0 300041.10 468 0.06 5.82 Molasses D 5960 72.80 20700.0 2520 44.30 552 0.054.50 Low pol sugar C 1130 9.46 4910.0 590 10.80 50 0.02 1.65 Low polsugar D 1290 15.50 4400.0 547 12.30 78 0.03 1.39 Foam C 83 24.80 309.077 7.06 6 0.03 1.27 Foam D 107 68.30 313 63.00 7 11.30 0.11 1.69 MixedJuice C 192 45.50 845.0 224 17.10 6 0.05 1.36 Mixed Juice D 160 86.80611.0 107 13.80 16 0.07 1.07 Raw sugar 94 0.51 67.5 28 0.65 <=.05 <=.0050.01

Example 9

In this example, sugar products containing GI lowering substancesaccording to the invention were prepared.

A high pol sugar base was prepared containing 98.88% sucrose (24.72 g),0.07% glucose (0.0175 g) and 0.07% fructose (0.0175 g). The term “pol”refers to the level of sucrose in sugar products. High pol describesproducts with at least 98.5% sucrose. Any product with less than 98.5%sucrose is referred to as “low pol”.

A low pol sugar base was prepared containing 88.5% sucrose (22.125 g),1.42% glucose (0.355 g) and 1.55% fructose (0.3875 g).

Formulation A: high pol sugar base was combined with 20% added molassesextract as prepared in Example 3 above. Formulation A has 79.104%sucrose (19.776 g), 0.056% glucose (0.014 g) and 0.056% fructose (0.014g).

Formulation B: high pol sugar base was combined with 20% galactose (5g). Formulation B has 79.104% sucrose (19.776 g), 0.056% glucose (0.014g) and 0.056% fructose (0.014 g).

Formulation C: low pol sugar base was combined with 20% galactose (5 g).Formulation C has 70.8% sucrose (17.7 g), 1.136% glucose (0.284 g) and1.24% fructose (0.31 g)

Example 10

In this example, the effect of the addition of organic acids to the pHand taste of high pol sugar was investigated.

Procedure

Molasses organic acid extract: A mixture of organic acids extracted frommolasses was prepared and had the following composition (18.2 mg oforganic acids can be extracted from 1 gram of molasses solids):

Organic acid Amount(g) cis-aconitic 2 citric 1 phosphoric 0.7 gluconic0.5 malic 1.5 trans-aconitic 12 succinic 0.3 lactic 0.2 cis-aconitic 2

This solution was added to 50 g of the high pol sugar base from Example9 at four levels of addition, equivalent to 1%, 2%, 5% and 10% molassesacids in sugar (m/v).

The mixtures were dissolved in water to a final volume of 500 mL.

The control contained the high pol sugar base with no added molassesacids.

Results

The pH of each formulation was tested.

Amount of added organic acid (% m/v) pH 0 6.62 1 5.45 2 4.87 5 4.08 103.66 Molasses organic acid extract 1.68

The results are plotted in FIG. 10.

The taste was tested by 5 tasters. The testers reported that all of thesamples tasted sweet. There was very little difference in taste betweenthe control and the formulations containing 1%, 2% and 5% of themolasses organic acid extract. However, the formulation with 10% of themolasses organic acid extract was slightly less sweet and had adifferent taste with a slightly sour/bitter aftertaste.

Conclusion

Up to 5% of molasses organic acid extract can be added to high pol sugarbase without interfering with the taste of the sweetener.

Example 11

This example investigates the glycaemic index of sweeteners preparedaccording to the invention.

Formulations Tested

Six (6) treatments were prepared for GI testing at the Human NutritionUnit, University of Sydney.

The High Pol Sucrose used in the treatments comprised 99% total sucrose,glucose and fructose (wherein the amount of glucose and fructose was nomore than 0.5%) and 1% of a mixture of organic acids, minerals,polyphenols, antioxidants and polysaccharides. This mixture consisted ofthe following:

-   -   600 to 2100 micrograms per gram of a mixture of trans-aconitic        acid, oxalic, cis-aconitic, citric, phosphoric, gluconic, malic,        succinic, lactic, formic and acetic acids, wherein most of the        mixture consisted of trans-acotinic acid in an amount in the        range from 200 to 600 micrograms per gram;    -   150 to 600 micrograms per gram of minerals with the ratio of        calcium to magnesium to potassium being 50:15:35;    -   0.2 to 0.5 mg catechin equivalents per gram of polyphenols;    -   antioxidants so that the antioxidant activity is in the range of        0.4 to 1.2 micromoles per gram; and    -   20 to 60 micrograms per gram of polysaccharides.

1 High Pol Sucrose alone 2 Low Pol Sucrose alone (contains more freeglucose than High Pol Sucrose) 3 High Pol Sucrose plus galactose in a4:1 ratio 4 Low Pol Sucrose plus galactose in a 4:1 ratio 5 High PolSucrose plus molasses extract from Example 3 in a 5:1 ratio 6 High PolSucrose plus molasses extract from Example 3 in a 2.5:1 ratio

Treatments 1 to 4 contained base sugar±galactose to give a 50 gcarbohydrate load (500 mL test solution). Sixteen (16) samples wereprepared per treatment: fifteen (15) for GI testing; and one (1)retained by QDPI&F.

Base Galactose Treat- (Average Standard (average Standard ment Baseweight) deviation weight) deviation 1 High Pol 50.495 0.001 — — Sucrose2 Low Pol 54.666 0.002 — — Sucrose 3 High Pol 40.236 0.001 10.160 0.003Sucrose 4 Low Pol 43.482 0.006 10.151 0.004 Sucrose

The carbohydrate loads in these treatments are shown below.

Carbohydrate load Treatment (average) Standard deviation 1 50.000 0.0012 50.003 0.002 3 50.002 0.003 4 49.924 0.005

Treatments 5 and 6 were prepared with two levels of molasses extractfrom Example 3 to give a carbohydrate load of 25 g (250 mL testsolution). Eleven (11) samples were prepared per formulation: ten (10)for GI testing; and one (1) retained by QDPI&F.

High Pol Standard Polyphenol (Average Standard Treatment Sucrosedeviation weight) deviation 5 25.254 0.003 4.975 0.022 6 25.253 0.0049.986 0.025

The carbohydrate loads in these treatments are shown below.

Treatment Carbohydrate load (average) Standard deviation 5 25.004 0.0036 25.002 0.004

Controls & Ingredients

Product Formulation Notes Glucose 100% glucose (glucodin) Supplied bySydney Uni control 10 × 50 g samples High Pol 98.88% sucrose Sucrosesupplied by MCM Sucrose 0.07% glucose 0.07% fructose 10 × 50 g samplesLow Pol 88.5% sucrose Sucrose supplied by MCM Sucrose 1.42% glucose1.55% fructose 10 × 50 g samples Galactose 10 g galactose Galactosesupplied by DPI&F

Glycemic Index (GI) Test Methods

This study was conducted by the Human Nutrition Unit at the Universityof Sydney using internationally recognised GI methodology, which hasbeen validated by results obtained from small experimental studies andlarge multi-centre research trials. The experimental procedures used inthis study were in accordance with international standards forconducting ethical research with humans and were approved by the HumanResearch Ethics Committee of Sydney University.

Experimental Procedures

Using standard methodology to determine a food's GI value, a portion ofthe food containing between 10 and 50 grams of available carbohydrate isfed to 10 healthy people the morning after they have fasted for 10-12hours overnight. A fasting blood sample is first obtained from eachperson and then the food is consumed, after which additional bloodsamples are obtained at regular intervals during the next two hours. Inthis way, it's possible to measure the total increase in blood sugarproduced by that food over a two-hour period. The two-hour blood glucose(glycaemic) response for this test food is then compared to the two-hourblood glucose response produced by the same amount of carbohydrate inthe form of pure glucose sugar (the reference food: GI value ofglucose=100%). Therefore, GI values for foods and drinks are relativemeasures (i.e. they indicate how high blood sugar levels rise aftereating a particular food compared to the very high blood sugar responseproduced by the same amount of carbohydrate in the form of glucosesugar). Equal-carbohydrate portions of test foods and the reference foodare used in GI experiments, because carbohydrate is the main componentin food that causes the blood's glucose level to rise.

The night before each test session, the subjects ate a regular low-fatevening meal based on a carbohydrate-rich food, other than legumes, andthen fasted for at least 10 hours overnight. The subjects were alsorequired to avoid alcohol and unusual levels of food intake and physicalactivity for the whole day before each test session.

The next morning, the subjects reported to the research centre in afasting condition. On arrival, the investigators first checked that thesubjects were well and had complied with all of the precedingexperimental conditions. The subjects then warmed a hand in hot waterfor one minute, after which two fasting finger-prick blood samples (−5and 0 minutes) were obtained (a few drops of blood; sampled twice) usingan automatic, non-reusable lancet device (Safe-T-Pro, BoehringerMannheim Gmbh, Mannheim, Germany). After the second fasting blood sample(0 minutes) was obtained, the subjects were seated at a table and givena fixed portion of the reference food or the test food, which theyconsumed together with 250 grams of plain water at a comfortable pacewithin 12 minutes. A stopwatch was started for each subject as soon asthey started eating. The subjects were required to remain at theresearch centre for the next two hours during which additional bloodsamples were collected at 15, 30, 45, 60, 90 and 120 minutes aftereating had commenced. Therefore, a total of eight blood samples werecollected from each subject during each two-hour test session.

Measurement of the Subjects' Blood Glucose Responses

For each subject, the concentration of glucose in each of the eightwhole blood samples collected from them during each test session wasanalysed in duplicate using a HemoCue® B-glucose photometric analyseremploying a glucose dehydrogenase/mutarotase enzymatic assay (HemoCueAB, Ängelholm, Sweden). Each blood sample was collected into a plasticHemoCue® cuvette containing the enzymes and reagents for the bloodglucose assay and then placed into the HemoCue analyser while theenzymatic reaction took place. Therefore, each blood sample was analysedimmediately after it was collected.

For each of the 10 subjects, a two-hour blood glucose response curve wasconstructed for each of their test sessions using the average bloodglucose concentrations for each of their eight blood samples. The twofasting blood samples were averaged to provide one baseline glucoseconcentration. The area under each two-hour blood glucose response curve(AUC) was then calculated in order to obtain a single number, whichindicates the total increase in blood glucose during the two-hour testperiod in that subject as a result of ingesting that food. A glycaemicindex (GI) value for each test sugar was then calculated for eachsubject by dividing their two-hour blood glucose AUC value for the testfood by their average two-hour blood glucose AUC value for the referencefood and multiplying by 100 to obtain a percentage score. GI value fortest food (%)=(Blood glucose AUC value for the test food)/(Average AUCvalue for the equal carbohydrate portion of the reference food)*100.

Due to differences in body weight and metabolism, blood glucoseresponses to the same food or drink can vary between different people.The use of the reference food to calculate GI values reduces thevariation between the subjects' blood glucose results to the same foodarising from these natural differences. Therefore, the GI value for thesame food varies less between the subjects than their glucose AUC valuesfor this food.

TABLE 18 The mean ± SEM GI values for the test foods and the referencefood tested using a 50-gram equal carbohydrate portion (n = 9). TestFood GI value (%) GI category Treatment 1 53 ± 5 Low GI Treatment 2 69 ±5 Moderate GI Glucose - 100 ± 0  High GI Reference Food

TABLE 19 The mean ± SEM GI values for the test foods and the referencefood tested using a 50-gram equal carbohydrate portion (n = 9). TestFood GI value (%) GI category Treatment 4 55 ± 7 Low GI Treatment 2 69 ±5 Moderate GI Glucose - 100 ± 0  High GI Reference Food

TABLE 20 The mean ± SEM GI values for the two test foods and thereference food tested using a 25-gram equal carbohydrate portion (n =9). Test Food GI value (%) GI category Treatment 6 51 ± 6 Low GITreatment 5 58 ± 6 Moderate GI Glucose - 100 ± 0  High GI Reference food

CONCLUSIONS

The results show that the various sweeteners of the invention have a lowGI. In particular, the use of a complex carbohydrate such as galactosewhen added to sugar reduces the GI to a low level. Further, the use of amolasses extract will also reduce the GI of sugar to a low level. Theword ‘comprising’ and forms of the word ‘comprising’ as used in thisdescription and in the claims does not limit the invention claimed toexclude any variants or additions. Modifications and improvements to theinvention will be readily apparent to those skilled in the art. Suchmodifications and improvements are intended to be within the scope ofthis invention.

The claims defining the invention are as follows:
 1. A sweetener havinga low GI comprising: (a) a sugar base comprising 97% to 99% of a mixtureconsisting of sucrose, glucose and fructose wherein the combined amountof glucose and fructose is no more than 0.5% w/w of the total sweetener;and (b) an extract derived from sugar cane comprising: (i) one or moreorganic acids selected from the group consisting of transaconitic acid,oxalic, cis-aconitic, citric, phosphoric, gluconic, malic, succinic,lactic, formic and acetic acids, wherein the total amount of acids inthe sweetener is an amount in the range from 600 to 2100 micrograms pergram; (ii) one or more minerals selected from the group consisting ofcalcium, magnesium and potassium, wherein the amount of minerals is inthe range from 150 to 600 micrograms per gram; (iii) one or morepolyphenols in an amount in the range from 0.2 to 0.5 mg catechinequivalents per gram; (iv) one or more antioxidants wherein theantioxidant activity is in the range of 0.4 to 1.2 micromoles per gram;and (v) one or more polysaccharides in the range from 20 to 60micrograms per gram.
 2. The sweetener according to claim 1 wherein theone or more organic acids is a mixture consisting of 2 partscis-acotonic acid, 1 part citric acid, 0.7 part phosphoric acid, 0.5part gluconic acid, 1.5 parts malic acid, 12 parts trans aconitic acid,0.3 part succinic acid and 0.2 part lactic acid.
 3. The sweetener ofclaim 1, wherein the amount of trans-aconitic acid forms the majority ofthe organic acids and is in an amount in the range from 200 to 600micrograms per gram.
 4. A sweetener having a low GI comprising: (a) asugar base comprising 97% to 99% of a mixture consisting of sucrose,glucose and fructose wherein the combined amount of glucose and fructoseis no more than 1.0% w/w of the total sweetener; and (b) an extractderived from sugar cane comprising: (i) one or more organic acidsselected from the group consisting of transaconitic acid, oxalic,cis-aconitic, citric, phosphoric, gluconic, malic, succinic, lactic,formic and acetic acids, wherein the total amount of acids in thesweetener is an amount in the range from 600 to 2100 micrograms pergram; (ii) one or more minerals selected from the group consisting ofcalcium, magnesium and potassium, wherein the amount of minerals is inthe range from 150 to 600 micrograms per gram; (iii) one or morepolyphenols in an amount in the range from 0.2 to 0.5 mg catechinequivalents per gram; (iv) one or more antioxidants wherein theantioxidant activity is in the range of 0.4 to 1.2 micromoles per gram;and (v) one or more polysaccharides in the range from 20 to 60micrograms per gram.
 5. The sweetener of claim 4, wherein the amount oftrans-aconitic acid forms the majority of the organic acids and is in anamount in the range from 200 to 600 micrograms per gram.